Layla

Layla (you may remember it as Ask Layla) is the chatty one. Tell it dates, budget and what kind of traveler you are, and it writes a day-by-day itinerary with live prices attached, pulling flight and hotel data through partners like Skyscanner, Booking.com, GetYourGuide and Viator. The company says over two million trips have been planned this way, and the product has matured from novelty chatbot into something families and honeymooners genuinely use end to end.

Two things distinguish it from the pack. First, multi-city and road trip routing is a real strength; it thinks in sequences, not just single destinations. Second, when the logistics outgrow the robot, you can hand the thread to a human travel expert for bookings and complicated connections. That escape hatch is rare in this category and worth knowing about for trips with moving parts.

Money matters

Full itineraries are free. What the $49-a-year tier actually buys, per Layla's own comparison, is live pricing from Skyscanner and Booking.com plus PriceLock alerts, so the free version plans the trip and the paid one prices and watches it. Bookings flow through affiliate partners, which is how the free half stays free.

Who owns it now

Worth knowing before you follow a booking link: Layla acquired Trip Planner AI, and Expedia Group acquired Layla in July 2026. Both now sit inside the same travel giant, which is not automatically bad (Expedia's supply is enormous) but is context you deserve when a recommendation points somewhere. Venue details deserve the usual double-check before you build a day around them, and travelers who want everything bookable in one interface may prefer Mindtrip, which keeps more of the transaction in-house.

Bottom line

The best conversational planner for multi-stop trips, with a human fallback nobody else in the free tier bracket offers. Just expect the message caps to nudge you toward the subscription if you plan often.